US4935241A - Pharmaceutical preparation for tinea pedis - Google Patents

Pharmaceutical preparation for tinea pedis Download PDF

Info

Publication number
US4935241A
US4935241A US07/266,894 US26689488A US4935241A US 4935241 A US4935241 A US 4935241A US 26689488 A US26689488 A US 26689488A US 4935241 A US4935241 A US 4935241A
Authority
US
United States
Prior art keywords
tinea pedis
pharmaceutical preparation
ccz
treatment
preparation
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
US07/266,894
Other languages
English (en)
Inventor
Izumi Saitoh
Kaori Ikeda
Shigeru Kido
Yoshio Doi
Shohei Egawa
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Shionogi and Co Ltd
Original Assignee
Shionogi and Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Shionogi and Co Ltd filed Critical Shionogi and Co Ltd
Assigned to SHIONOGI & CO., LTD., 12, 3-CHOME, DOSHO-MACHI, HIGASHI-KU, OSAKA, JAPAN reassignment SHIONOGI & CO., LTD., 12, 3-CHOME, DOSHO-MACHI, HIGASHI-KU, OSAKA, JAPAN ASSIGNMENT OF ASSIGNORS INTEREST. Assignors: DOI, YOSHIO, EGAWA, SHOHEI, IKEDA, KAORI, KIDO, SHIGERU, SAITOH, IZUMI
Application granted granted Critical
Publication of US4935241A publication Critical patent/US4935241A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Images

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/415—1,2-Diazoles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
    • A61K47/32—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. carbomers, poly(meth)acrylates, or polyvinyl pyrrolidone
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
    • A61K47/36—Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
    • A61K47/38—Cellulose; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0014—Skin, i.e. galenical aspects of topical compositions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders

Definitions

  • the present invention relates to external preparations of croconazole hydrochloride (hereinafter abbreviated as CCZ) known as an antifungal agent.
  • CCZ croconazole hydrochloride
  • CCZ is a potent antifungal agent which has been developed and marketed as cream- or gel-type preparations under the trade name of Pilzcin® by Shionogi & Co., Ltd, and is enjoying wide popularity.
  • the present invention provides pharmaceutical preparations for the treatment of tinea pedis, containing as basic components about 0.1% to about 2.5% of croconazole hydrochloride and about 1%-15% of an ethyl acrylate-methyl methacrylate copolymer in an aqueous alcohol, and if necessary, about 0.1%-2.5% of a thickening agent and/or a plasticizer.
  • the ordinate shows CCZ amount in the skin, while the abscissa shows time.
  • the remaining amount of CCZ in the skin are shown by the marks " ⁇ " for the control and " ⁇ " for the Example 1 preparation.
  • the present inventors tried to provide sustained release preparations of CCZ for tinea pedis which would form a soft and strong coating film on the affected parts without the use of any extra additive such as a softening agent; and thus completed the present invention.
  • the percentages of materials used indicate the percentages by weight (w/w%) of the materials to the total weight of the whole preparation.
  • This invention can be achieved by dissolving about 0.1%--about 2.5% of CCZ and about 1%--about 15% of a copolymer of ethyl acrylate and methyl methacrylate (hereinafter abbreviated as EA-MMA) in an aqueous alcohol. If necessary, about 0.1%--about 2.5% of a thickening agent and/or a plasticizer may be further added. Eudragit®E30D may be a good representative for EA-MMA.
  • the aqueous alcohol used in this invention means a mixture of a lower alkanol and purified water. Lower alkanol includes, for example, ethanol, propanol, isopropanol, and the like. Aqueous alcohols whose alcohol content is between about 55% and 75% are preferably employed.
  • thickening agents such cellulose derivatives as ethyl cellulose (EC), hydroxypropyl cellulose (HPC) and hydroxypropylmethyl cellulose (HPMC) are preferably used; and as plasticizers, propylene glycol (PG), polyethylene glycol (PEG), etc., are preferably used.
  • the tinea pedis preparations of this invention enhance the transdermal absorbability of CCZ and make drug effectiveness last for a long time. So, it can be expected that once a day application of the preparation is enough to attain good efficacy.
  • tinea pedis preparations consisting of such components as shown in Table 1 were obtained.
  • the numeral shown in the table indicates how much the component was used (% by weight).
  • the rat is fixed on its back, and then an absorption chamber (application area: 10 cm 2 ) is fixed on the surface of the hairless abdomen with an binder.
  • a pre-fixed dose of a test material (3 mg as CCZ per rat) is placed into the chamber.
  • the coating film formed on the skin in the chamber is peeled off with distilled water and collected into suitable vessel.
  • the chamber is removed and the application area of the skin is cut off.
  • the sample in Item 4 and the piece of the skin in Item 5 are employed for the CCZ content measurement by HPLC.
  • MA.EA Copolymer of methacrylic acid and ethyl acrylate
  • DMAEM.ME Copolymer of dimethylaminoethyl methacrylate and ester of methacrylic acid
  • Control * 1% Pilzcin® Cream (made by Shionogi & Co., Ltd.)
  • the transdermal absorbability of CCZ varied greatly with the sorts of the high molecular substances used as base materials.
  • the preparations A and B in which MA.EA and DMAEM.ME were used respectively showed lower transdermal absorbabilities of CCZ.
  • the preparation C in which EM.MMA employed in this invention was used showed an equal or a higher transdermal absorbability than that in the control preparation.
  • Example 1 The preparation of Example 1 was compared with the control preparation (1% Pilzcin Cream: commercially available) as to how long the drug effectiveness would last.
  • the CCZ amount in the skin was measured at several points of time according to the aforementioned test method.
  • the preparation of this invention suppressed the maximum concentration in the skin and, at the same time, prolonged the time to reach there: this is the typical aspect seen in every sustained release preparation. Furthermore, the preparation of this invention showed a remarkably high value in AUC (area under the curve), the fact of which demonstrates a high bioavailability of CCZ.

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Inorganic Chemistry (AREA)
  • Dermatology (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Organic Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicinal Preparation (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
US07/266,894 1987-12-08 1988-11-03 Pharmaceutical preparation for tinea pedis Expired - Lifetime US4935241A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP62-310479 1987-12-08
JP62310479A JPH0818983B2 (ja) 1987-12-08 1987-12-08 水虫治療剤

Publications (1)

Publication Number Publication Date
US4935241A true US4935241A (en) 1990-06-19

Family

ID=18005734

Family Applications (1)

Application Number Title Priority Date Filing Date
US07/266,894 Expired - Lifetime US4935241A (en) 1987-12-08 1988-11-03 Pharmaceutical preparation for tinea pedis

Country Status (8)

Country Link
US (1) US4935241A (ko)
EP (1) EP0319965B1 (ko)
JP (1) JPH0818983B2 (ko)
KR (1) KR960009415B1 (ko)
AT (1) ATE61522T1 (ko)
DE (1) DE3862017D1 (ko)
ES (1) ES2036661T3 (ko)
GR (1) GR3001862T3 (ko)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998023291A1 (en) * 1996-11-22 1998-06-04 Soltec Research Pty. Ltd. Percutaneous delivery system
US20030228382A1 (en) * 2002-06-06 2003-12-11 Dr. Ivar Roth Foot Fixer Kit
WO2004010988A1 (en) * 2002-07-31 2004-02-05 Connetics Australlia Pty Ltd Percutaneous and perungual delivery system
US20100168200A1 (en) * 2007-09-05 2010-07-01 Pola Pharma Inc. Antifungal pharmaceutical composition
US8481591B2 (en) 2010-11-01 2013-07-09 Stiefel Research Australia Pty. Ltd. Polymeric topical compositions
US10278928B2 (en) 2013-02-13 2019-05-07 Dong-A Pharmaceutical Co., Ltd Film-forming pharmaceutical composition for wound healing and method for preparing the same

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0794378B2 (ja) * 1989-08-18 1995-10-11 久光製薬株式会社 エアゾール剤
SG166105A1 (en) 2005-09-29 2010-11-29 Novartis Ag Antifungal composition
KR20140027319A (ko) * 2011-05-26 2014-03-06 노파르티스 아게 생리학상 활성제의 경피 투여를 위한 조성물

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4619826A (en) * 1983-05-23 1986-10-28 The Dow Chemical Company Acne control method
US4803066A (en) * 1986-03-22 1989-02-07 Smith & Nephew Associated Companies P.L.C. Antibacterial and/or antifungal compositions for topical application

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4619826A (en) * 1983-05-23 1986-10-28 The Dow Chemical Company Acne control method
US4803066A (en) * 1986-03-22 1989-02-07 Smith & Nephew Associated Companies P.L.C. Antibacterial and/or antifungal compositions for topical application

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
Chemical Abstracts 104: 10582w (1986). *
USAN and USP Dictionary of Drug Names, p. 153 (1989). *

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998023291A1 (en) * 1996-11-22 1998-06-04 Soltec Research Pty. Ltd. Percutaneous delivery system
US6211250B1 (en) 1996-11-22 2001-04-03 Soltec Research Pty Ltd. Percutaneous delivery system
KR100551930B1 (ko) * 1996-11-22 2006-02-16 코네틱스 오스트레일리아 피티와이 리미티드 경피 전달계
US20030228382A1 (en) * 2002-06-06 2003-12-11 Dr. Ivar Roth Foot Fixer Kit
WO2004010988A1 (en) * 2002-07-31 2004-02-05 Connetics Australlia Pty Ltd Percutaneous and perungual delivery system
US20050175641A1 (en) * 2002-07-31 2005-08-11 Connetics Australia Pty Ltd Percutaneous and perungual delivery system
US20100168200A1 (en) * 2007-09-05 2010-07-01 Pola Pharma Inc. Antifungal pharmaceutical composition
US9480678B2 (en) * 2007-09-05 2016-11-01 Pola Pharma Inc. Antifungal pharmaceutical composition
US8481591B2 (en) 2010-11-01 2013-07-09 Stiefel Research Australia Pty. Ltd. Polymeric topical compositions
US8841351B2 (en) 2010-11-01 2014-09-23 Stiefel Research Australia Pty Ltd. Polymeric topical compositions
US10278928B2 (en) 2013-02-13 2019-05-07 Dong-A Pharmaceutical Co., Ltd Film-forming pharmaceutical composition for wound healing and method for preparing the same

Also Published As

Publication number Publication date
ATE61522T1 (de) 1991-03-15
EP0319965B1 (en) 1991-03-13
ES2036661T3 (es) 1993-06-01
DE3862017D1 (de) 1991-04-18
JPH01149725A (ja) 1989-06-12
EP0319965A1 (en) 1989-06-14
KR890009391A (ko) 1989-08-01
KR960009415B1 (ko) 1996-07-19
GR3001862T3 (en) 1992-11-23
JPH0818983B2 (ja) 1996-02-28

Similar Documents

Publication Publication Date Title
KR100367150B1 (ko) 손발톱진균증치료용손발톱니스제및그제조방법
US20030049307A1 (en) Pharmaceutical composition
KR20000069044A (ko) 경피 전달계
JP2001521886A (ja) プロスタグランジンｅ１送達のための局所組成物
JPH05279247A (ja) 徐放性液剤
CA2400178A1 (en) Nail lacquer pharmaceutical composition
AU2001243189A1 (en) Pharmaceutical composition
PT503988E (pt) Composicoes para o tratamento de onicomicoses
EP2043604A2 (en) Topical compositions
US4935241A (en) Pharmaceutical preparation for tinea pedis
US4915940A (en) Film-formation-type antifungal preparation
JPH06211651A (ja) 爪白癬治療用組成物
EP1446093B1 (en) Potentiated topical composition
JPH0572368B2 (ko)
KR960008315B1 (ko) 외용 겔 기제
JP3472359B2 (ja) チミペロン含有貼付剤
JPH111433A (ja) トルナフテ−ト含有液剤
JPH0478620B2 (ko)
SK500562022A3 (sk) Lekárska náplasť s pomalým uvoľňovaním
JP4209488B2 (ja) 皮膚創傷治療剤
WO2018116190A1 (en) Topical sprayable compositions of ketorolac tromethamine
KR20000013593A (ko) 피록시캄의 경피투여 조성물
PT95825B (pt) Processo para a preparacao de composicoes farmaceuticas para a administracao transdermica contendo 2-amino-6-n-propilamino-4,5,6,7-tetra-hidrobenzotriazol

Legal Events

Date Code Title Description
AS Assignment

Owner name: SHIONOGI & CO., LTD., 12, 3-CHOME, DOSHO-MACHI, HI

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST.;ASSIGNORS:SAITOH, IZUMI;IKEDA, KAORI;KIDO, SHIGERU;AND OTHERS;REEL/FRAME:004993/0324

Effective date: 19881017

STCF Information on status: patent grant

Free format text: PATENTED CASE

FEPP Fee payment procedure

Free format text: PAYOR NUMBER ASSIGNED (ORIGINAL EVENT CODE: ASPN); ENTITY STATUS OF PATENT OWNER: LARGE ENTITY

FPAY Fee payment

Year of fee payment: 4

FPAY Fee payment

Year of fee payment: 8

FPAY Fee payment

Year of fee payment: 12